Homes in ZIP Code 04364

• 

  

  

  /60

  $964,999

  • 6 Beds
  • 4 Baths
  • 6,493 Sq Ft

  172-B Annabessacook Rd, Winthrop, ME 04364

  FRESH SURVEY & TITLE COMPLETED and ready for quick closing! Now includes 20 sprawling acres and a 20-foot right of way to Annabessacook Lake! This custom-built executive estate blends resort-style amenities with refined finishes for the perfect mix of luxury and functionality. Originally completed in 1997 and beautifully renovated in 2019 and 2023, the home offers 6,493 SF of finely crafted

  

  Tim Dunham

  Tim Dunham Realty

  (207) 803-6219

  172-B Annabessacook Rd, Winthrop, ME 04364
• 

  

  

  /20

  $21,461 per month

  • 3 Beds
  • 1.5 Baths
  • Condo for Rent

  100 Woods Grove Ln Unit SI ID1255650P, Winthrop, ME 04364

  The advertised rate of $21,461/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 11, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it

  100 Woods Grove Ln Unit SI ID1255650P, Winthrop, ME 04364
• 

  

  /2

  $65,000 Sold Feb 23, 2026

  Lot 6 Holmes Brook Ln, Winthrop, ME 04364

  • Land
  • 10 Acres
  • $6,500 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 7 Days On Market

  Last Listing Agent Jane Gravel Blue Lobster Real Estate

  

  Lot 6 Holmes Brook Ln, Winthrop, ME 04364
• 

  

  

  /102

  Est $1,232,113 Not Listed For Sale

  24 Loch Ln, Winthrop, ME 04364

  • 4 Beds
  • 3.5 Baths
  • 3,712 Sq Ft
  • Built 1999

  

  24 Loch Ln, Winthrop, ME 04364

  Last Sold Summary

  • 1% Above List Price
  • $330/SF
  • 173 Days On Market

  Last Sold Price $1,225,000

  Last Listing Agent Stephanie Yeaton Gardner Portside Real Estate Group
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  /123

  $965,000

  • 6 Beds
  • 4 Baths
  • 6,493 Sq Ft

  172 Annabessacook Rd, Winthrop, ME 04364

  FRESH SURVEY AND TITLE COMPLETED and ready for quick closing! Now includes a 20-foot right of way to Annabessacook Lake and 20 sprawling acres!! This custom-built executive estate offers unparalleled luxury and comfort. A true one-of-a-kind haven, it blends resort-style amenities with high-end finishes for the perfect combination of elegance and functionality. Originally completed in 1997 and

  

  Tim Dunham

  Tim Dunham Realty

  (207) 367-3848

  

  172 Annabessacook Rd, Winthrop, ME 04364
• 

  

  /20

  $5,100 per month

  • 2 Beds
  • 1 Bath
  • 865 Sq Ft
  • House for Rent

  7 Fire Rd W24a, Winthrop, ME 04364

  Property Id: 1200423Cozy Keyes Cottage is a fully furnished, all-inclusive waterfront home located on the shores of prestigious Cobbosseecontee Lake in central Maine. Designed for mid-term stays of one month or longer, this cottage provides a comfortable, turnkey living solution for individuals and families who need a high-quality temporary residence without the complexity of managing

  7 Fire Rd W24a, Winthrop, ME 04364
• 

  

  /57

  $300,000 Sold Sep 15, 2025

  22 Old Route 133, Winthrop, ME 04364

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $206/SF
  • 4 Days On Market

  Last Listing Agent Rebecca Wilson Better Homes & Gardens Real Estate/The Masiello Group

  

  22 Old Route 133, Winthrop, ME 04364
• 

  

  /37

  Est $227,286 Not Listed For Sale

  87 Woodland Rd, Winthrop, ME 04364

  • 1 Bed
  • 2 Baths
  • 896 Sq Ft
  • Built 2004

  

  87 Woodland Rd, Winthrop, ME 04364

  Last Sold Summary

  • 30% Above List Price
  • $195/SF
  • 27 Days On Market

  Last Sold Price $175,000

  Last Listing Agent Pat Ladd Homestead Realty
• 

  

  /69

  $489,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft

  63 Maple Ridge Dr, Winthrop, ME 04364

  Welcome to 63 Maple Ridge Drive in Winthrop! Wonderful one owner, one level home in a beautiful neighborhood. Custom built home offering 3 bedrooms and two baths. Features include granite counters in the cooks kitchen with plenty of cabinets and stainless appliances. The living room has cozy wood fireplace surrounded by built ins, hardwood floors and walks out to a spacious and private deck. The

  

  Pat Ladd

  Homestead Realty

  (207) 806-5750

  

  63 Maple Ridge Dr, Winthrop, ME 04364
• 

  

  /13

  $4,400 per month

  • 1 Bed
  • 1 Bath
  • 810 Sq Ft
  • House for Rent

  11 Fire Rd W24a, Winthrop, ME 04364

  Property Id: 1200424Little Landing Cottage on Cobbosseecontee LakeLittle Landing Cottage is a fully furnished, all-inclusive waterfront home on the shores of prestigious Cobbosseecontee Lake — designed for comfort, convenience, and effortless living.This turnkey cottage includes every utility at no additional cost: high-speed internet (500+ Mbps), electricity, heat, hot

  11 Fire Rd W24a, Winthrop, ME 04364
• 

  

  /51

  $410,000 Sold Jun 23, 2025

  97 Pennwood Rd, Winthrop, ME 04364

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft
  • Built 1971

  Last Sold Summary

  • 10% Above List Price
  • $204/SF
  • 4 Days On Market

  Current Estimated Value $409,497

  Last Listing Agent Pat Ladd Homestead Realty

  

  97 Pennwood Rd, Winthrop, ME 04364
• 

  

  /47

  Est $1,094,289 Not Listed For Sale

  76 Pine Point Ln, Winthrop, ME 04364

  • 4 Beds
  • 3.5 Baths
  • 3,100 Sq Ft
  • Built 1975

  

  76 Pine Point Ln, Winthrop, ME 04364

  Last Sold Summary

  • 1% Above List Price
  • $348/SF
  • 6 Days On Market

  Last Sold Price $1,078,500

  Last Listing Agent Colin Harvey Legacy Properties Sotheby's International Realty
• 

  /2

  $65,000

  • Land
  • 26.55 Acres
  • $2,448 per Acre

  90 Bearce Rd, Winthrop, ME 04364

  Land and privacy!! Build your dream home and belong to Maple Ridge Owners Association and have the buffer of the green space making your home even more private. This is a great building lot. Lot #23.

  

  Pat Ladd

  Homestead Realty

  (207) 640-2322

  

  90 Bearce Rd, Winthrop, ME 04364
• 

  

  /33

  $330,000 Sold Jun 30, 2025

  96 Pamela Dr, Winthrop, ME 04364

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 1988

  Last Sold Summary

  • 8% Above List Price
  • $219/SF
  • 2 Days On Market

  Current Estimated Value $334,101

  Last Listing Agent Pat Ladd Homestead Realty

  

  96 Pamela Dr, Winthrop, ME 04364
• 

  

  /26

  Est $306,049 Not Listed For Sale

  262 Metcalf Rd, Winthrop, ME 04364

  • 2 Beds
  • 1 Bath
  • 1,184 Sq Ft
  • Built 1985

  

  262 Metcalf Rd, Winthrop, ME 04364

  Last Sold Summary

  • 13% Above List Price
  • $228/SF
  • 3 Days On Market

  Last Sold Price $270,000

  Last Listing Agent Roger Naylor Jr EXP Realty
• 

  

  /92

  $795,000

  • 2 Beds
  • 2 Baths
  • 2,470 Sq Ft

  882 Memorial Dr, Winthrop, ME 04364

  Maranacook Lake Living! Sunsets over the 165' of waterfront on this +/-7 mile Central Maine lake. The home sits at water's edge and comes with dock system, several west facing decks and terraces all for year round lakefront enjoyment. Beautiful home with tiled entries. The open custom oak kitchen/dining area is filled with sunlight and warmed by a propane fireplace. Additionally the main level

  

  Pat Ladd

  Homestead Realty

  (207) 672-2067

  

  882 Memorial Dr, Winthrop, ME 04364
• 

  

  /200

  $860,000 Sold Feb 05, 2026

  427 Mount Pisgah Rd, Winthrop, ME 04364

  • 3 Beds
  • 2.5 Baths
  • 3,672 Sq Ft
  • Built 1815

  Last Sold Summary

  • 9% Below List Price
  • $234/SF
  • 87 Days On Market

  Current Estimated Value $849,374

  Last Listing Agent Rick Bisson Keller Williams Realty

  

  427 Mount Pisgah Rd, Winthrop, ME 04364
• 

  

  /73

  Est $489,725 Not Listed For Sale

  91 Wedgewood Dr, Winthrop, ME 04364

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Built 1986

  

  91 Wedgewood Dr, Winthrop, ME 04364

  Last Sold Summary

  • 3% Above List Price
  • $170/SF
  • 28 Days On Market

  Last Sold Price $475,000

  Last Listing Agent Pat Ladd Homestead Realty
• 

  

  /43

  $399,900

  • 4 Beds
  • 3 Baths
  • 2,170 Sq Ft

  105 Nottingham Rd, Winthrop, ME 04364

  VIRTUAL TOUR AVAILABLE ONLINENestled on 2.5 private acres in the highly desirable Sherwood Forest Subdivision, this delightful Dutch Colonial offers space, charm, and opportunity--just minutes from downtown Winthrop. Classic in style and generous in layout, this 4-bedroom, 3-bath home is ready to welcome its next chapter. The first floor features a spacious eat-in kitchen with a cozy

  Nicholas Corrow Real Broker

  

  105 Nottingham Rd, Winthrop, ME 04364
• 

  

  /7

  $950,000 Sold Aug 08, 2025

  1385 U S 202, Winthrop, ME 04364

  • 19 Baths
  • 6,789 Sq Ft
  • Built 1958

  Last Sold Summary

  • 21% Below List Price
  • $140/SF
  • 11 Days On Market

  Last Listing Agent Benjamin Spencer CORE

  

  1385 U S 202, Winthrop, ME 04364
• 

  

  /36

  Est $335,711 Not Listed For Sale

  108 Pamela Dr, Winthrop, ME 04364

  • 3 Beds
  • 1 Bath
  • 1,913 Sq Ft
  • Built 1984

  

  108 Pamela Dr, Winthrop, ME 04364

  Last Sold Summary

  • 29% Above List Price
  • $136/SF
  • 2 Days On Market

  Last Sold Price $259,900

  Last Listing Agent Pat Ladd Homestead Realty
• 

  

  /60

  $485,000

  • 4 Beds
  • 2 Baths
  • 3,081 Sq Ft

  974 Sturtevant Hill Rd, Winthrop, ME 04364

  Imagine all the space you will have with this 10 room home. This home has been expanded over the years and provides one with so many options. There is even an insulated unfinished basement just waiting for your creative ideas. You have a spacious eat in kitchen, formal dining room, large living room and a den on the lower level. All bedrooms are on the main level. The primary bedroom with its own

  Merline Douglas Lakehome Group Real Estate

  

  974 Sturtevant Hill Rd, Winthrop, ME 04364
• 

  

  /29

  $250,000 Sold May 09, 2025

  57 Dexter Pond Rd, Winthrop, ME 04364

  • 1 Bed
  • 1 Bath
  • 489 Sq Ft
  • Built 1970

  Last Sold Summary

  • 11% Below List Price
  • $511/SF
  • 85 Days On Market

  Current Estimated Value $241,521

  Last Listing Agent Mark Michaud Fontaine Family-The Real Estate Leader

  

  57 Dexter Pond Rd, Winthrop, ME 04364
• 

  

  /59

  Est $398,974 Not Listed For Sale

  17 Pamela Dr, Winthrop, ME 04364

  • 3 Beds
  • 1.5 Baths
  • 2,878 Sq Ft
  • Built 1976

  

  17 Pamela Dr, Winthrop, ME 04364

  Last Sold Summary

  • 37% Above List Price
  • $101/SF
  • 7 Days On Market

  Last Sold Price $291,067

  Last Listing Agent Karen Ramsay-Boucher Better Homes & Gardens Real Estate/The Masiello Group
• 

  

  /52

  $559,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,395 Sq Ft

  476 Winthrop Center Rd, Winthrop, ME 04364

  Step into the perfect blend of historic character and modern comfort in this beautifully restored 1917 late‑Edwardian farmhouse, set proudly on a stunning Hallowell granite foundation. This 2,382 sq ft home showcases meticulously preserved original details, including restored pine floors throughout most of the first level, complemented by new matching pine in the kitchen and family room.

  Robert Whisenant RE/MAX Riverside

  

  476 Winthrop Center Rd, Winthrop, ME 04364
• 

  

  /45

  $325,000 Sold Jul 03, 2025

  39 Case Rd, Winthrop, ME 04364

  • 3 Beds
  • 1.5 Baths
  • 1,874 Sq Ft
  • Built 1957

  Last Sold Summary

  • 8% Above List Price
  • $173/SF
  • 4 Days On Market

  Current Estimated Value $317,484

  Last Listing Agent Jessica Fike Brookewood Realty

  

  39 Case Rd, Winthrop, ME 04364
• 

  

  /35

  Est $446,671 Not Listed For Sale

  310 Route 41, Winthrop, ME 04364

  • 4 Beds
  • 2 Baths
  • 2,072 Sq Ft
  • Built 2004

  

  310 Route 41, Winthrop, ME 04364

  Last Sold Summary

  • 6% Above List Price
  • $203/SF
  • 35 Days On Market

  Last Sold Price $421,000

  Last Listing Agent Mariea Thurlow United Country Lifestyle Properties of Maine
• 

  

  /98

  $649,000

  • 4 Beds
  • 3 Baths
  • 2,054 Sq Ft

  89 Boot Cove Ln, Winthrop, ME 04364

  This thoughtfully designed four-bedroom, three-bath ranch is tucked into a peaceful wooded setting with direct frontage on Lower Narrows Pond. This fresh and clean property creates a pleasant flow with recent updates, an expansive back deck, and hot tub overlooking the lake! A cozy wood stove in the lower level creates a memorable atmosphere! The private dock and a newly designed staircase

  Terri Levesque Amnet Realty

  

  89 Boot Cove Ln, Winthrop, ME 04364
• 

  

  /3

  $259,000 Sold Apr 24, 2025

  32 Winthrop Center Rd, Winthrop, ME 04364

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1963

  Last Sold Summary

  • $245/SF

  Current Estimated Value $268,986

  Last Listing Agent Ellen Wells Coldwell Banker Plourde Real Estate

  

  32 Winthrop Center Rd, Winthrop, ME 04364
• 

  

  /57

  Est $398,683 Not Listed For Sale

  15 Lakeshore Dr, Winthrop, ME 04364

  • 4 Beds
  • 1.5 Baths
  • 2,792 Sq Ft
  • Built 1974

  

  15 Lakeshore Dr, Winthrop, ME 04364

  Last Sold Summary

  • 4% Above List Price
  • $138/SF
  • 13 Days On Market

  Last Sold Price $384,500

  Last Listing Agent Pat Ladd Homestead Realty
• 

  

  /70

  $620,000

  • 5 Beds
  • 3 Baths
  • 3,704 Sq Ft

  307 Route 41, Winthrop, ME 04364

  This meticulously maintained farmhouse has been tastefully updated to preserve it's historic charm, all while adding modern improvements for ease and peace of mind. Built in 1784, the home boasts over 3700 square feet and three stories of living space, and features a custom kitchen with quartz countertops and a Queen Ann stove, a spacious first floor primary suite, and a gorgeous sunroom with

  Lori Dube Sprague & Curtis Real Estate

  

  307 Route 41, Winthrop, ME 04364
• 

  

  /20

  $14,000 Sold Oct 23, 2025

  35A-12 Woodland Rd, Winthrop, ME 04364

  • Land
  • 0.49 Acre
  • $28,571 per Acre

  Last Sold Summary

  • 49% Below List Price
  • 91 Days On Market

  Last Listing Agent Kimberly Granholm LAER

  

  35A-12 Woodland Rd, Winthrop, ME 04364
• 

  

  /32

  Est $257,226 Not Listed For Sale

  1006 Sturtevant Hill Rd, Winthrop, ME 04364

  • 3 Beds
  • 1.5 Baths
  • 907 Sq Ft
  • Built 1969

  

  1006 Sturtevant Hill Rd, Winthrop, ME 04364

  Last Sold Summary

  • 5% Above List Price
  • $270/SF
  • 30 Days On Market

  Last Sold Price $245,000

  Last Listing Agent Mark Michaud Fontaine Family-The Real Estate Leader
• 

  

  /43

  $499,000

  • 3 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  104 Memorial Dr, Winthrop, ME 04364

  Lakefront -waterfront- home facing west on the shores of Maranacook Lake. A great sunset location close to town with public water and sewer. This Cape has easy access and is waiting for your personal touches. The yard is a nice gentle slope to the water. Room for gardening and boats. Shorefront is a mix of some gravel and some sand. Beautiful swimming in summertime. Some of the best ice skating

  Sam Lambert Keller Williams Realty

  

  104 Memorial Dr, Winthrop, ME 04364
• 

  

  /53

  $415,000 Sold May 21, 2025

  345 Main St, Winthrop, ME 04364

  • 4 Beds
  • 2 Baths
  • 2,280 Sq Ft
  • Built 1964

  Last Sold Summary

  • $182/SF
  • 10 Days On Market

  Current Estimated Value $402,004

  Last Listing Agent Shawn McKillop Maine Real Estate Co

  

  345 Main St, Winthrop, ME 04364
• 

  

  /36

  Est $346,134 Not Listed For Sale

  30 Route 41, Winthrop, ME 04364

  • 4 Beds
  • 1.5 Baths
  • 1,798 Sq Ft
  • Built 1971

  

  30 Route 41, Winthrop, ME 04364

  Last Sold Summary

  • 13% Above List Price
  • $170/SF
  • 12 Days On Market

  Last Sold Price $305,000

  Last Listing Agent Lori Gray Homestead Realty
• 

  

  /12

  $199,999

  • Land
  • 64.81 Acres
  • $3,086 per Acre

  616 Stanley Rd, Winthrop, ME 04364

  Surveyed Buildable lot with 1.8 acre of land to have a homestead, hunt and recreational activities. the rest of the land is enrolled in Tree Growth but can be taken out. Septic, drilled well and electricity already at the site. Come bring your vision to own one of the largest lots in Winthrop.

  Dawn Lopez Hearth & Key Realty

  

  616 Stanley Rd, Winthrop, ME 04364
• 

  

  /47

  $320,000 Sold Oct 27, 2025

  170 Hathaway Rd, Winthrop, ME 04364

  • 3 Beds
  • 2 Baths
  • 2,575 Sq Ft
  • Built 1850

  Last Sold Summary

  • 11% Below List Price
  • $124/SF
  • 210 Days On Market

  Current Estimated Value $333,331

  Last Listing Agent Heidi Libby NextHome Northern Lights Realty

  

  170 Hathaway Rd, Winthrop, ME 04364
• 

  

  /30

  Est $539,171 Not Listed For Sale

  20 Maranacook Station Ln, Winthrop, ME 04364

  • 3 Beds
  • 1 Bath
  • 1,542 Sq Ft
  • Built 1900

  

  20 Maranacook Station Ln, Winthrop, ME 04364

  Last Sold Summary

  • 12% Above List Price
  • $311/SF
  • 40 Days On Market

  Last Sold Price $480,000

  Last Listing Agent Katherine Davis Thomas Agency
• 

  

  /19

  $89,900

  • Land
  • 3.11 Acres
  • $28,907 per Acre

  0 U S Highway 202, Winthrop, ME 04364

  Incredible opportunity to live or build right next to Winthrop High School and Middle School—walk to both! This former apple orchard offers 3.1 acres with two access points: one through Apple Farm Crossing and the other directly off Route 202. Zoned for residential use, with public water and sewer available, it's a prime location with great visibility and road frontage on Route 202. Ideal for a

  Brian Rizzo Rizzo Mattson

  

  0 U S Highway 202, Winthrop, ME 04364

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